US4129724A - 9-Deoxy-9-methylene-PGF-3,4-didehydropiperidylamides - Google Patents
9-Deoxy-9-methylene-PGF-3,4-didehydropiperidylamides Download PDFInfo
- Publication number
- US4129724A US4129724A US05/894,268 US89426878A US4129724A US 4129724 A US4129724 A US 4129724A US 89426878 A US89426878 A US 89426878A US 4129724 A US4129724 A US 4129724A
- Authority
- US
- United States
- Prior art keywords
- prostaglandin analog
- analog according
- deoxy
- methylene
- pgf
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000003180 prostaglandins Chemical class 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- -1 inclusive Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002831 pharmacologic agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
Definitions
- the present application is a continuation-in-part of Ser. No. 786,250, filed Apr. 11, 1977, now U.S. Pat. No. 4,098,805.
- the present invention relates to novel 9-deoxy-9-methylene-PFG, 3,4-didehydropiperidylamides, the essential material constituting a disclosure of which is incorporated here by reference from U.S. Pat. No. 4,098,805.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to novel 9-deoxy-9-methylene-PGF ,3,4-didehydropiperidylamides. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding 9-deoxy-9-methylene-PFG-type acids.
Description
This application is a continuation-in-part of Ser. No. 786,250, filed Apr. 11, 1977, now U.S. Pat. No. 4,098,805, issued July 4, 1978.
The present application is a continuation-in-part of Ser. No. 786,250, filed Apr. 11, 1977, now U.S. Pat. No. 4,098,805. The present invention relates to novel 9-deoxy-9-methylene-PFG, 3,4-didehydropiperidylamides, the essential material constituting a disclosure of which is incorporated here by reference from U.S. Pat. No. 4,098,805.
Claims (32)
1. A prostaglandin analog of the formula ##STR1## wherein Y1 is trans--CH═CH--, --C.tbd.C--, or --CH2 CH2 --
wherein M1 is ##STR2## wherein R5 is hydrogen or methyl; WHEREIN L1 is ##STR3## or a mixture of ##STR4## wherein R3 and R4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R3 and R4 is fluoro only when the other is hydrogen or fluoro;
Wherein Z2 is
(1) --(CH2)3 --(CH2)g --CH2 --,
(2) --(ch2)3 --(ch2)g --CF2 --,
(3) --ch2 --o--ch2 --(ch2)g --CH2 --,
(4) --c.tbd.c--ch2 --(ch2)g --CH2 --,
(5) --ch2 --c.tbd.c--(ch2)g --CH2 --,
(6) ##STR5## WHEREIN G IS ONE, 2 OR 3; WHEREIN R7 is
(1) --(CH2)m --CH3, ##STR6## WHEREIN M IS ONE TO 5, INCLUSIVE, H IS ZERO OR ONE, T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, and s is zero, one, 2, to 3, the various T's being the same or different, with the proviso that not moe than two T's are other than alkyl, with the further proviso that R7 is ##STR7## wherein T and s are as defined above, only when R3 and R4 are hydrogen or methyl, being the same or different; and
wherein R21 and R22 are hydrogen, alkyl of one to 12 carbon atoms, inclusive; aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 3 carbon atoms, inclusive, or phenyl substituted with hydroxycarbonyl or alkoxycarbonyl of one to 4 carbon atoms, inclusive.
2. A prostaglandin analog according to claim 1, wherein Y1 is --C.tbd.C--.
3. 9-Deoxy-9-methylene-13,14-didehydro-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 2.
4. A prostaglandin analog according to claim 1, wherein Y1 is --CH2 CH2 --.
5. 9-Deoxy-9-methylene-13,14-dihydro-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 4.
6. A prostaglandin analog according to claim 1, wherein Y1 is trans-CH=CH--.
7. A prostaglandin analog according to claim 6, wherein Z2 is aromatic.
8. 9-Deoxy-9-methylene-3,7-inter-m-phenylene-3oxa-4,5,6-trinor-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 7.
9. 9-Deoxy-9-methylene-3,7-inter-m-phenylene-4,5,6-trinor-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 7.
10. A prostaglandin analog according to claim 6, wherein Z2 is aliphatic.
11. A prostaglandin analog according to claim 10, wherein M1 is ##STR8##
12. 15-epi-9-deoxy-9-methylene-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 11.
13. A prostaglandin analog according to claim 10, wherein M1 is ##STR9##
14. A prostaglandin analog according to claim 13, wherein Z2 is cis--CH═CH--CH2 --(CH2)g --CH2 --.
15. A prostaglandin analog according to claim 14, wherein R7 is ##STR10##
16. 9-Deoxy-9-methylene-17-phenyl-18,19,20-trinor-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 15.
17. A prostaglandin analog according to claim 14, wherein R7 is ##STR11##
18. 9-Deoxy-9-methylene-16-phenoxy-17,18,19,20-tetranor-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 17.
19. A prostaglandin analog according to claim 14, wherein R7 is --(CH2)m --CH3.
20. A prostaglandin analog according to claim 19, wherein m is 3.
21. A prostaglandin analog according to claim 20, wherein g is 3.
22. 2a,2b-Dihomo-9-deoxy-9-methylene-15-methyl-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 21.
23. A prostaglandin analog according to claim 20, wherein g is one.
24. A prostaglandin analog according to claim 23, wherein at least one of R3 and R4 is methyl.
25. 9-Deoxy-9-methylene-16,16-dimethyl-PGF1,3,4-didehydropiperidylamide, a prostaglandin analog according to claim 24.
26. A prostaglandin analog according to claim 23, wherein at least one of R3 and R4 is fluoro.
27. 9-Deoxy-9-methylene-16,16-difluoro-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 26.
28. A prostaglandin analog according to claim 23, wherein R3 and R4 are both hydrogen.
29. A prostaglandin analog according to claim 28, wherein R5 is methyl.
30. 9-Deoxy-9-methylene-15-methyl-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 29.
31. A prostaglandin analog according to claim 28, wherein R5 is hydrogen.
32. 9-Deoxy-9-methylene-PGF1, 3,4-didehydropiperidylamide, a prostaglandin analog according to claim 31.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/786,250 US4098805A (en) | 1977-04-11 | 1977-04-11 | 9-deoxy-9-methylene-pgf-type amides |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/786,250 Continuation-In-Part US4098805A (en) | 1977-04-11 | 1977-04-11 | 9-deoxy-9-methylene-pgf-type amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4129724A true US4129724A (en) | 1978-12-12 |
Family
ID=25138056
Family Applications (11)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/786,250 Expired - Lifetime US4098805A (en) | 1977-04-11 | 1977-04-11 | 9-deoxy-9-methylene-pgf-type amides |
| US05/894,273 Expired - Lifetime US4129727A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -pyrrolidylamides |
| US05/894,216 Expired - Lifetime US4127569A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -hexamethyliminoamides |
| US05/894,270 Expired - Lifetime US4129726A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -piperizinylamides |
| US05/894,269 Expired - Lifetime US4129725A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -pyrrolinylamides |
| US05/894,272 Expired - Lifetime US4130720A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF-p-substituted phenyl esters |
| US05/894,271 Expired - Lifetime US4130584A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF sulfonylamides |
| US05/894,215 Expired - Lifetime US4128712A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -morpholinylamides |
| US05/894,214 Expired - Lifetime US4145534A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PFG1 -piperidylamides |
| US05/894,268 Expired - Lifetime US4129724A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF-3,4-didehydropiperidylamides |
| US05/899,663 Expired - Lifetime US4137403A (en) | 1977-04-11 | 1978-04-24 | 9-Deoxy-9-methylene-PGF2 cycloamides |
Family Applications Before (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/786,250 Expired - Lifetime US4098805A (en) | 1977-04-11 | 1977-04-11 | 9-deoxy-9-methylene-pgf-type amides |
| US05/894,273 Expired - Lifetime US4129727A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -pyrrolidylamides |
| US05/894,216 Expired - Lifetime US4127569A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -hexamethyliminoamides |
| US05/894,270 Expired - Lifetime US4129726A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -piperizinylamides |
| US05/894,269 Expired - Lifetime US4129725A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -pyrrolinylamides |
| US05/894,272 Expired - Lifetime US4130720A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF-p-substituted phenyl esters |
| US05/894,271 Expired - Lifetime US4130584A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF sulfonylamides |
| US05/894,215 Expired - Lifetime US4128712A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PGF1 -morpholinylamides |
| US05/894,214 Expired - Lifetime US4145534A (en) | 1977-04-11 | 1978-04-07 | 9-Deoxy-9-methylene-PFG1 -piperidylamides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/899,663 Expired - Lifetime US4137403A (en) | 1977-04-11 | 1978-04-24 | 9-Deoxy-9-methylene-PGF2 cycloamides |
Country Status (8)
| Country | Link |
|---|---|
| US (11) | US4098805A (en) |
| JP (1) | JPS53127438A (en) |
| BE (1) | BE865882A (en) |
| CH (1) | CH635072A5 (en) |
| DE (1) | DE2814710A1 (en) |
| FR (1) | FR2387217A2 (en) |
| GB (1) | GB1568018A (en) |
| NL (1) | NL7803434A (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4169895A (en) * | 1976-09-28 | 1979-10-02 | Pfizer Inc. | Antisecretory 16,16-dimethyl-17-oxaprostaglandins |
| US4118584A (en) * | 1977-04-11 | 1978-10-03 | The Upjohn Company | 9-Deoxy-9-methylene-16-phenyl-PGF compounds |
| US4276435A (en) * | 1979-04-02 | 1981-06-30 | The Upjohn Company | 19,20-Didehydro-PG1, sulfonyl amides |
| US4264524A (en) * | 1979-04-02 | 1981-04-28 | The Upjohn Company | 19,20-Didehydro-PG1 amides |
| US4278812A (en) * | 1979-04-02 | 1981-07-14 | The Upjohn Company | 19,20-Didehydro-PG2 sulfonyl amides |
| US4283351A (en) * | 1979-04-02 | 1981-08-11 | The Upjohn Company | 19,20-Didehydro-13,14-dihydro-PG2 amides |
| US4264522A (en) * | 1979-04-02 | 1981-04-28 | The Upjohn Company | 19-Hydroxy-PG amides |
| US4276434A (en) * | 1979-04-02 | 1981-06-30 | The Upjohn Company | 19,20-Didehydro-13,14-dihydro-PG1, sulfonyl amides |
| US4283350A (en) * | 1979-04-02 | 1981-08-11 | The Upjohn Company | 19,20-Didehydro-PG2 amides |
| US4264523A (en) * | 1979-04-02 | 1981-04-28 | The Upjohn Company | 19,20-Didehydro-13,14-dihydro-PG1 amides |
| US4278813A (en) * | 1979-04-02 | 1981-07-14 | The Upjohn Company | 19,20-Didehydro-13,14-dihydro-PG2, sulfonyl amides |
| US4292444A (en) * | 1980-02-08 | 1981-09-29 | Pfizer Inc. | Sulfonyl prostaglandin carboxamide derivatives |
| US4349690A (en) * | 1981-04-23 | 1982-09-14 | The Upjohn Company | 9-Deoxy-9-methylene-6-keto-PGE-type compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954741A (en) * | 1972-06-07 | 1976-05-04 | Pfizer Inc. | N-substituted prostaglandin carboxamides |
| US3981868A (en) * | 1973-05-31 | 1976-09-21 | American Cyanamid Company | Derivatives of 9-oxo-13-trans-prostenoic acid amides |
| FR2239458A1 (en) * | 1973-07-31 | 1975-02-28 | Aries Robert | Prostaglandin amides - with antilipolytic, gonadotrophic, luteolytic, hypotensive and other activities associated with prostaglandins |
| US3890372A (en) * | 1974-01-08 | 1975-06-17 | Upjohn Co | Amino substituted phenyl and naphthyl esters of PGF{HD 2{301 {B - type compounds |
| US3927197A (en) * | 1974-04-19 | 1975-12-16 | Pfizer | Tertiary alcohol stabilized E-series prostaglandins |
| US4060534A (en) * | 1976-01-23 | 1977-11-29 | The Upjohn Company | 9-Deoxy-9-methylene-PGF compounds |
| US4118584A (en) * | 1977-04-11 | 1978-10-03 | The Upjohn Company | 9-Deoxy-9-methylene-16-phenyl-PGF compounds |
-
1977
- 1977-04-11 US US05/786,250 patent/US4098805A/en not_active Expired - Lifetime
-
1978
- 1978-03-09 GB GB9340/78A patent/GB1568018A/en not_active Expired
- 1978-03-31 NL NL7803434A patent/NL7803434A/en not_active Application Discontinuation
- 1978-04-05 DE DE19782814710 patent/DE2814710A1/en not_active Withdrawn
- 1978-04-07 US US05/894,273 patent/US4129727A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,216 patent/US4127569A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,270 patent/US4129726A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,269 patent/US4129725A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,272 patent/US4130720A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,271 patent/US4130584A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,215 patent/US4128712A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,214 patent/US4145534A/en not_active Expired - Lifetime
- 1978-04-07 US US05/894,268 patent/US4129724A/en not_active Expired - Lifetime
- 1978-04-10 FR FR7810582A patent/FR2387217A2/en active Granted
- 1978-04-10 CH CH384578A patent/CH635072A5/en not_active IP Right Cessation
- 1978-04-11 JP JP4184678A patent/JPS53127438A/en active Pending
- 1978-04-11 BE BE186717A patent/BE865882A/en not_active IP Right Cessation
- 1978-04-24 US US05/899,663 patent/US4137403A/en not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
|---|
| derwent Abstract 16389U-B, NL 7211860-Q, 05-03-78. * |
| Derwent Abstract 75530X/40, US 3981868, 21-09-76. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US4128712A (en) | 1978-12-05 |
| JPS53127438A (en) | 1978-11-07 |
| US4098805A (en) | 1978-07-04 |
| US4130584A (en) | 1978-12-19 |
| FR2387217A2 (en) | 1978-11-10 |
| US4145534A (en) | 1979-03-20 |
| DE2814710A1 (en) | 1978-10-12 |
| US4129727A (en) | 1978-12-12 |
| US4137403A (en) | 1979-01-30 |
| US4129725A (en) | 1978-12-12 |
| NL7803434A (en) | 1978-10-13 |
| BE865882A (en) | 1978-10-11 |
| GB1568018A (en) | 1980-05-21 |
| FR2387217B2 (en) | 1981-04-30 |
| CH635072A5 (en) | 1983-03-15 |
| US4129726A (en) | 1978-12-12 |
| US4130720A (en) | 1978-12-19 |
| US4127569A (en) | 1978-11-28 |
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